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Isobutylamine → (Rac)-(6-isobutylamino-imidazo[1,2-b]pyridazin-3-yl)-quinolin-6-yl-methanol

HRID 69175
ノート
印刷プレビュー

反応式

HRID 69175 の反応式
Cl[C:2]1[CH:3]=[CH:4][C:5]2[N:6]([C:8]([CH:11]([C:13]3[CH:14]=[C:15]4[C:20](=[CH:21][CH:22]=3)[N:19]=[CH:18][CH:17]=[CH:16]4)[OH:12])=[CH:9][N:10]=2)[N:7]=1.[F-].[K+].[CH2:25]([NH2:29])[CH:26]([CH3:28])[CH3:27]>CN1C(=O)CCC1.CC(OC)(C)C>[CH2:25]([NH:29][C:2]1[CH:3]=[CH:4][C:5]2[N:6]([C:8]([CH:11]([C:13]3[CH:14]=[C:15]4[C:20](=[CH:21][CH:22]=3)[N:19]=[CH:18][CH:17]=[CH:16]4)[OH:12])=[CH:9][N:10]=2)[N:7]=1)[CH:26]([CH3:28])[CH3:27]
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

6

反応物 3

HCID 6558IsobutylamineHCID 522689Potassium FluorideHCID 87524298(6-Chloroimidazo[1,2-b]pyridazin-3-yl)(quinolin-6-yl)methanol

生成物 1

HCID 44208574(Rac)-(6-isobutylamino-imidazo[1,2-b]pyridazin-3-yl)-quinolin-6-yl-methanol

試薬・触媒・溶媒 2

HCID 13387N-methyl-2-pyrrolidone溶媒
HCID 15413
tert-Butyl methyl ether
溶媒

反応条件

温度
160 °C

実験手順

(rac)-(6-chloro-imidazo[1,2-b]pyridazin-3-yl)-quinolin-6-yl-methanol (Stage 1.1, 80 mg, 0.257 mmol) and KF (30 mg, 0.515 mmol) were suspended in NMP (2 mL). Isobutylamine (129 μL, 1.287 mmol) was then added and the RM was stirred at 160° C. for 7 h. The mixture was diluted with TBME and washed with water (3×). The aqueous layer was then extracted with TBME (3×). The combined layers were dried over Na2SO4, filtered and concentrated. The residue was purified by flash chromatography (Flashmaster) to afford the title compound as a yellow foam (tR 4.11 min (conditions 4), MH+=348.0, 1H-NMR in DMSO-d6: 8.86 (m, 1H); 8.32 (m, 1H); 8.02 (m, 1H); 7.94 (d, 1H); 7.80 (m, 1H); 7.61 (d, 1H); 7.51 (dd, 1H); 7.31 (s, 1H); 6.88 (t, 1Ht); 6.61 (d, 1H); 6.24 (m, 1H); 6.12 (d, 1H); 2.98 (m, 2H); 1.82 (m, 1H); 0.86 (m, 6H)).

後処理

  1. washwashed with water (3×)
  2. extractionThe aqueous layer was then extracted with TBME (3×)
  3. dry with materialThe combined layers were dried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe residue was purified by flash chromatography (Flashmaster)

出典と根拠

ORDレコード
ord-8783c27a2cc24dc389f649d4f5c1c640
出典データセット
uspto-grants-2014_09
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08822468B2

反応ノート

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